Methanol → Methyl p-tolylacetate

HRID 1439796Notes

Reaction equation

HRID 1439796 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[CH3:10][O-:11].[Na+].[OH2:13].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:22]O>[Mn]>[CH3:10][O:11][C:22](=[O:13])[CH2:6][C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1.[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:10]([OH:13])=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 962WaterHCID 77224-Methylbenzyl chlorideHCID 24489Sodium DithioniteHCID 10942334Sodium Methoxide

Product 2

HCID 90265Methyl p-tolylacetateYield 57.2%HCID 248474p-Tolylacetic acidYield 8%

Reagents, catalysts & solvents 1

HCID 23930ManganeseCatalyst

Procedure

In the manner described in Example 1, 70.5 g (0.5 mole) of p-methylbenzyl chloride and 135 g of a 24 wt-% sodium methylate solution in methanol, 5 g CoCl2.6 H2O, 4 g manganese powder and 1 g sodium dithionite were reacted with CO. The reaction and the processing were performed as described in Example 1. 47.0 g of p-methylphenylacetic acid methyl ester (BP13 113°) (yield 57.2%) was isolated in a purity of 98%, plus 6.2 of p-methylphenylacetic acid (MP 89°-90° C, yield 8%).

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-15aeb649a09f4e5c8655617c85483753
Source dataset
uspto-grants-1977_11
Patent number
US04060690

Reaction notes

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